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  When he gave the students copies of Orwell’s essay, he asked them to annotate it with their questions and comments. After they had read it and discussed it, he collected the marked-up copies and graded the annotations. There were no passive elements in his class—not the texts, which were constantly being worked over, nor the students, who conferred in groups and revved or critiqued one another. Mr. Leon read their journals on a regular basis. He told them again and again that they would not get good marks for participation just by raising their hand a lot. They had to keep their notebooks open, take down what was happening in class. They were busy. So was he, and my mind and body quailed at the amount of work he did for this class, which was only one of four (two tenth grade, two twelfth grade) that he taught four times a week. After class, he occasionally munched on a power bar. “I’m going on faux energy,” he told me once. Maybe, but I couldn’t tell the difference.

  He was driving them out of laziness and routine the way a coach challenges and drills a football team. Hating loose conversation, he made the students bring one set of ideas to bear on another, one quotation to bear on another. He required them to ask questions of each other along a common theme. “I’m interested in the psychology of who calls on whom,” he said to me, and in that way he thought of the class as an organic being, forever redefining itself. In general, their contributions had to be connected, nailed, referenced, specific. Education in the humanities was all about intellectual charting—fitting and joining, marking and connecting, and, of course, those ever-useful high school exercises, comparing and contrasting.

  But how do you compare one thing with another? By describing object A completely and then object B? Or by going point by point, back and forth, between the two objects? Every newspaper columnist, fitting his titanic argument into eight hundred words, has faced this awful problem. The latter—going back and forth—was the prescribed high school way. All through the discussion of 1984, Mr. Leon was setting up the kids for a compare-and-contrast essay with Brave New World. At one point, just to get the comparative juices flowing, he asked two students to volunteer as objects to be compared and contrasted. Marco and Lena, grinning wildly, stood in the center of the room. The other students ran through Marco and Lena’s shapes, bodies, hair color, clothes, attitudes. Slender and slender; curly and brown, curly and very brown; black and white sneakers, pink and white sneakers. Compared and contrasted, the two of them glowed like actors on the red carpet.

  Sean Leon combined basic intellectual instruction with short, vibrant talks on the ethics of being a student. There was, forever, the sore topic of SparkNotes, the online “study aid” which no doubt obsessed half the English teachers in America. SparkNotes was a thorough and competent guide to classic works, including 1984, so competent that it removed the necessity of reading books for students all over the country. When Mr. Leon made these remarks, another online aid, Shmoop, was just getting going. Shmoop’s online site boasted, in a chorus of little kids, “WE SPEAK STUDENT,” and it offered guides to the classics in short animated videos with pop-up graphics and nauseating colloquial language. On 1984, Shmoop held forth as follows: “In the future, life kinda sucks.” Shmoop dissolved literature into popular culture altogether.

  “Know this,” Mr. Leon said. “If you are relying on SparkNotes—and I know some of you are—it jumps out of your journals and your comments. If you read it in lieu of the text or take an interpretation from it, know that I know. I will never call you out in class. I don’t mind if you use it to help you understand the text, a difficult stretch, but reading SparkNotes in place of the book is problematic.”

  He led the students up the mountain at times, but he also kept the tent pegged to the ground.

  * * *

  Mr. Leon’s students still had the freedom to create themselves as individuals, if they would seize it. 1984, published in 1949, was the book most powerfully devoted to the opposite condition—an absence of freedom so complete that its existence was rapidly becoming impossible to conceive of. As two generations knew, Orwell’s bitterly satirical dystopian novel, along with his earlier satire, Animal Farm, in which pigs make a revolution that slips into dictatorship—“All animals are equal, but some animals are more equal than others”—the two Orwell books had, along with Arthur Koestler’s Darkness at Noon (1940), done more to discredit Soviet communism in the West than any other texts. (Solzhenitsyn’s The Gulag Archipelago wasn’t published in the West until 1973.) Reading 1984 again, I was eager to see if it seemed dated and overwrought—or merely lurid and masochistic.

  To my surprise, I was more moved by it than I had been in high school. The hero, Winston Smith, an Outer Party member living in drab, dreary, cold, smelly London, capital of “Airstrip One,” as Orwell calls it, works at the Ministry of Truth, where his job is to keep the past in sync with an ever-changing present—he rewrites and then files old newspaper articles. At home, he’s assaulted by the TV screen, which is able to observe him while blaring party propaganda and exhortations from Big Brother, the ageless and probably nonexistent leader whose face and commands are everywhere. Winston Smith! With his physical debility, his varicose veins, his forlorn happy memories of childhood, his belief in the proletariat, whom the party ignores; his disgust, his hopes, his doomed “rebellious” love affair with a fellow worker at the Ministry, dark-haired, avid Julia—Winston was the sad intelligent Everyman of totalitarian society, a sputtering flame who suspects that he’s the last conscious man alive.

  Orwell published Animal Farm at the end of the Second World War; the book caused a sensation, and in the next few years he wrote dozens of articles and essays as well as 1984. Yet the late forties was not a happy time for him. One totalitarian power was still in place, and it was rapidly taking over Eastern Europe. Orwell himself was falling apart from tuberculosis and other ills, which he intentionally aggravated by living much of the time in the damp and cold climate of Jura, in the Hebrides Islands. He was consciously heading toward death, a man tied, emotionally, to shabbiness and decay, as if these things had some truth in themselves that he needed to visit over and over. Yet, if he was familiar—too familiar—with pain, he had not relinquished his indignation over it. As a novelist, Orwell doesn’t compare to D. H. Lawrence, James Joyce, Virginia Woolf, E. M. Forster, or the Ian McEwan of Atonement, but his grindingly earnest and passionately angry book has endured. There were far worse fates for a novel than becoming an ideology-destroying text and a high school classic.

  Many of Mr. Leon’s students, as far as I could see, knew little twentieth-century history, though Mr. Leon assumed that they were familiar with Nazism and the destruction of the European Jews. He told them briefly about Soviet purges in which “millions were killed for shadowy reasons,” and asked them, as before, to do basic research on the Internet. They needed to read up. The ideological struggles of the twentieth century were a long way from them, and the struggle against Islamic fundamentalism was still in its early stages—not an emotional fact in their lives, though they had strong sentiments against unwinnable American fights in Afghanistan and Iraq. They wanted to get a good job, lead a good life, maybe do something useful, but they were not politically motivated—or even, as far as I could see, much interested—as my friends and I were as teenagers.

  Mr. Leon, however, asked them to study Orwell’s densely written invention, “Goldstein’s book,” a gift to Winston from the treacherous party intellectual O’Brien, who wants to ensnare Winston into subversion. The book, created by the party, is both a history of twentieth-century authoritarianism and a detailed tract explaining the necessity of single-party rule, a state of permanent war, unending surveillance, reduced consciousness leading to the destruction of the self—the entire panoply of totalitarian measures ruling Orwell’s dystopia. It’s a dangerous, truth-telling text. This was the students’ education in the totalitarian temptation. They broke into groups, discussing how Goldstein’s book crashed into contemporary politics. Justin mentioned C
hina’s restriction of Internet traffic, Jared Bennett the easiness of killing people with drones halfway around the world.

  Mr. Leon moved away from history and took up his usual cross-hatching of questions and responses. Ike, the round-faced boy who spoke little, asked Susanna, “Who accuses Winston of thoughtcrime?” and Susanna then asked Vanessa, “What is Winston writing in his journal?” and so on. The conversation moved to Winston’s character, and several students cited Winston’s incoherent despair, early in the novel, as he sits before his diary, knowing that whatever he writes, or doesn’t write, it will have no effect at all—“down with big brother they always shoot you in the back of the neck i don’t care down with big brother.” They traced his passage from that nullity to something like contentment and a more settled political purpose after meeting Julia. “She still expected something from life,” Winston says of her. “She would not accept it as a law of nature that the individual is always defeated.” A debate broke out over Julia’s role—whether she had made him more determined to rebel or merely happy, and a few of the girls found him “selfish,” which surprised me. Justin disagreed. “Relationships like this are so few and far between,” he said mournfully. Winston, after all, is grabbing at the only moments of happiness he will ever know.

  I had heard similar complaints before. A number of the girls—Maud, Marina, in particular—seemed irritated with the male characters who dominated these fictions. Marina even accused Winston of wanting personal power, of wanting “to replace Big Brother,” which seemed way off. It was obvious enough what was behind the exasperation. Minister Hooper, Bernard Marx, now Winston. Mr. Leon’s books were neither written by women nor featured women (except for crazy Miss Emily in Faulkner’s story). The girls in the class did not challenge the reading list, but some sort of displeasure came through.

  Sean Leon was drawn to writing that defined life in existential terms—Who are you? How will you live?—and, apart from Sylvia Plath, the writers he favored were all men. Which raised an old, very sore issue. Until recently, women had been discouraged from heroic composition in the arts, and, often enough, the crises that women wrote about in fiction were grounded in the material circumstances of life. Yet millions of readers knew that the issues were just as momentous. Jane Austen’s marital comedies, which are devoted, among other things, to perception, ethics, risk, and self-knowledge, as well as manners, class, property—the novels certainly ask, amid the many delights they offer, how one should live one’s life. (The evolutionary biologist Richard Dawkins made a fool of himself in a New York Times interview, of September 12, 2013, by dismissing Pride and Prejudice as unworthy of his time. “I can’t get excited about who is going to marry whom, and how rich they are.” Not all philistines are as advanced in evolutionary terms as Professor Dawkins.) Mr. Leon might have assigned Pride and Prejudice. He might also have assigned Charlotte Bronte’s tumultuous Jane Eyre. But both novels were written in the nineteenth century, and he wanted to keep the list modern. He assigned Hawthorne, whose sense of universal guilt anticipated Kafka, and Dostoevsky, who might be said to anticipate the future, but everything else was from the twentieth century. He might have assigned Edith Wharton’s The House of Mirth, but Wharton is perhaps too worldly for fifteen-year-olds. He might have assigned Willa Cather’s Song of a Lark or her story “Paul’s Case.” The class might have read stories by Charlotte Perkins Gilman or Katherine Anne Porter or Flannery O’Connor or Alice Munro.

  When I mentioned the issue to him, he admitted it was a problem that he had never been able to solve. He said he had thought at various times of assigning Kate Chopin’s The Awakening, written in 1899 and set in his home state, Louisiana, and also Simone De Beauvoir’s 1967 novella, “The Woman Destroyed.” De Beauvoir’s tale features a woman who is married to a cheater but can’t leave him. Sean Leon had taught it in twelfth grade, but “the women students were angry at the wife, not at the straying husband.” That was the end of that, and he wound up rejecting both books for tenth grade. The Awakening, the story of a married woman’s sexual and emotional arousal, would be awkward—intrusive, almost—as a subject for teenagers. Moral issues, yes; spiritual and existential issues, yes. Sex, no.

  He taught Faulkner and Hawthorne, Plath, Huxley, and Orwell. Later in the year, he would teach Paulo Coelho and Herman Hesse, Kurt Vonnegut, Viktor Frankl, Dostoevsky, Sartre, and Beckett, which, all in all, was a formidable list for tenth-graders. He was introducing them to modernism, both as a literary movement and as a mood. He was passionate about those books, and he tried to get the students excited about them, which was what counted most. Tenth grade, his class, was the beginning of their serious reading lives, a time of planting circuits. Intensity mattered more than inclusiveness.

  * * *

  In his happiest moments, Winston speaks of the proletarians—or “proles,” as Orwell called them—as the hope of the future. But it became clear the students didn’t know what the word meant. The Marxist rhetoric Orwell used satirically was foreign to them. Its time had passed. So Mr. Leon turned to a passage—both sorrowful and sympathetic—that describes the proles from Winston’s point of view.

  They were born, they grew up in the gutters, they went to work at twelve, they passed through a brief blossoming period of beauty and sexual desire, they married at twenty, they were middle-aged at thirty, they died, for the most part, at sixty. Heavy physical work, the care of home and children, petty quarrels with neighbors, films, football, beer, and above all, gambling filled up the horizon of their minds. To keep them in control was not difficult.

  “How is it possible,” Mr. Leon said, “that a major part of the population would not take issue with Big Brother? Why are they not rising up?”

  Unhappy Justin said, “They don’t know any better,” and Maud, whose remarks sometimes came off as haughty, said that “they are content.” Outer Party members like Winston were monitored every second, but the proles were able to enjoy sex, have kids, lead a normal life. They had the elements of a working-class culture—newspapers, movies, old songs. In some ways, Maud was right.

  “Think of the parallels with our world,” Mr. Leon said. He mentioned a Hispanic student from two years earlier who brought up the situation of poor Latinos in the United States. “He railed against the bad publications on the newsstands, the lottery in the bodegas. He was very provocative,” and suddenly Marco, as if picking up the torch from the earlier student, said, “They don’t put anything in the newspapers, so they don’t hear about anything real. They give them the sport, the crime.” By “they,” he meant the publishers of El Diario la Prensa, the big Spanish-language paper in New York. Marco had jumped in with such remarks before. His horsing around in class was a defense, I thought, against the earnest guy underneath.

  The students latched onto a moving passage late in the book—Winston’s admiration for a large, red-faced, working-class woman busy in the yard below the small room in which he and Julia meet. The woman has had many children, many sorrows, and never stops working. When Winston and Julia look at her, she is singing—the only active unpoliced culture in the book. “Her appearance shows how much experience of life she had,” said plaintive Vanessa, who had a good bit of experience of life herself. Her mother was Chinese (born here), her father was Puerto Rican; they had split up recently, and she lived with her dad on Delancey Street, in a bad neighborhood. “My mom would scream a lot,” she told me when I spoke to her. “I know she loved me, but I wanted to break free from her. I left my little sister behind, and I feel guilty about that. But when I’m with her, it’s chaos. It’s going sky-diving in my own head.” She appreciated the hardihood of the woman in the yard; her own mother was failing her, refusing to support her plans to go to college, and it was tearing at her. Vanessa’s life was almost unbearably freighted. Her tearful state, her sense of being oppressed in some way, grated on me at the beginning of the year, but she had more than earned her sadness. After I understood this, I rooted for her to triumph over it.
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br />   Jordan, also in appreciation of the woman in the yard, added, “She shows what is necessary to keep love alive,” which was a key point in 1984, in which the party does its best to destroy family love, sexual love—anything not directed at the party and Big Brother.

  “Out of those mighty loins,” Winston thinks, “a race of conscious beings must one day come. You were the dead; theirs was the future.” And Orwell goes on as follows:

  “We are the dead,” [Winston] said.

  “We are the dead,” echoed Julia dutifully.

  “You are the dead,” said an iron voice behind them.

  “What happens to Winston Smith at the end of the novel?” Mr. Leon asked, and together they went through the frightening scenes in which the sadistic O’Brien torments Winston, breaking down his resolve with electric current and brutal logic. Several of them returned to Goldstein’s book: O’Brien had given it to Winston in order to fully enlighten him, and then to destroy him that much more thoroughly. Marina, coming around on Winston, said that Goldstein’s book, which lays out the forms of totalitarianism, “shows that Winston isn’t psychotic.”

  At the end, Winston, annihilated by pain and fear, betrays Julia. “Why does it matter that he loved—or didn’t love Julia?” Mr. Leon asked. Marisa, who had seen, in Brave New World, the destruction of the individual, said, “If you love, you become a person,” which was exactly the point. The person—the self—is what O’Brien destroys. Earlier, Winston had hoped to die loathing Big Brother and the party. But the last sentence of the book—“He loved Big Brother”—tells us his spiritual annihilation has been completed. In the end, they understood what had happened to Winston.